In 2007, Matthew Weiner was a writer who had just wrapped up work on The Sopranos, taking a risk by bringing his new show—some niche period piece about advertising in the ’60s—to AMC, a basic-cable channel known for airing classic movies that had not, to that point, been the home of any original TV dramas.

Oh, how things have changed. Eight years later, AMC is a big part of what many see as television’s golden era, and that’s in large part because of the remarkable success of Weiner’s Mad Men. Far more than a show that celebrates the glamour in boozing, smoking, and womanizing—though there’s hedonism in there, to be sure—Mad Men has been an intoxicating brew of cerebral, tense storytelling about a remarkable cultural moment in America, made-to-measure with immaculate attention to historical detail. And its impact on the culture has been significant: We have Mad Men to thank for, at least in part, the increased popularity of men’s fashion, a return to 60s-era grooming, and a renewed interest in cocktail culture.

But it all ends on May 17. What will happen to Don Draper, the show’s brooding ad man with a dark secret?

In the first half of our Canadian-exclusive conversation with the showrunner, Weiner told Maclean’s why he’s been using the show to play with the idea of identity, why Don Draper is so compulsively watchable, and why the books on the show may not hold the clues to the ending, after all. Here, Weiner goes on the record about the fan theory that has the Internet buzzing, why he doesn’t think the ending is all that important, and his “special connection to Canada.”

I want to pin you down specifically on one fan theory, which is the D.B. Cooper one, I’m sure you’ve heard that—the idea that Don is the mysterious man who, in 1971, hijacked a plane, robbed everyone, and then jumped out of the plane, never to be seen again.

Yes and … here’s the thing. Again, not symbolic. Literal. In the premiere of season 7, Don was with Megan in California and Lost Horizon was playing on the television set and what happened is that I had seen the movie while I was writing. It was written right before World War II and there’s this wonderful opening to it, which is from the [1933] book, which is, “In times of war,” or, you know, “Rumours of war.” The movie Lost Horizon was not a tremendous success, but I saw this movie, felt it was so poetic and so related to Don’s situation, and I was like, “Could we put it on TV? Was it playing on the late show at any point?” And we actually found a date within the window of when that first episode was supposed to be set where it was playing two or three times in Los Angeles and New York on the late show so I just felt it was, to quote another movie, kismet. And when you see it referenced again there in the title it’s about heading toward a disaster and dreaming of paradise.

But very specifically for people who want to read into it, the movie is about a plane hijacking, really.

But it’s not related to D.B. Cooper, I hate to say it. I love—I mean you’ll have to watch the show, maybe I’m lying to you—but I love that people care enough to posit these things. I think it’s fantastic and that’s all I can say. It’s a huge compliment to us. But I’m never—what’s the word—I’m never trolling the audience, I’m never baiting them to create a theory. Sometimes when I do make it clear, like after that T-shirt controversy [fans developed a theory that Megan Draper was doomed to die because she wore the same shirt as the murdered actress Sharon Tate] then I get accused of more trolling. I don’t even know what to say.

Yeah, I’m afraid I am. I love that people care but I also think that there’s a real desire for the audience to anticipate the ongoing story and feel that they have guessed it and gotten it right and anything where they do feel like they’re right, they seem to say that the show is obvious and poorly constructed, and anything where they get it wrong, they think that I’m reacting to them.

We have a writers’ room of 10 people, and we’re trying to tell a story to entertain people, and the episodes toward the end of any season do pay off, but I always want to make it clear that the journey is the point, you know? The story starts on page one—it doesn’t start on page 50. People, from what I can tell, really enjoyed last week’s episode [the third-to-last episode], but I don’t think they understand that Joan coming into a showdown with McCann-Erickson is not possible unless we tell the story of where we’re going. Don walking out of that meeting is not possible without him encountering Diana. There’s information being given that’s not about the continuing story, that’s about the characters. So on the one hand I love that they’re doing it, on the other hand, it’s not on my mind at all, not even slightly. I mean, I’m here to entertain them, I do want it to be twists and turns, but it’s not on my mind at all. Is that disappointing?

—And I think you’re right. Well, certainly you are, you created the show.

[Laughs]

Joan Holloway, played by Christina Hendricks, talks with Mad Men creator Matthew Weiner on the set of the show’s second season. (Carin Baer/AMC)

I was struck by something that Jon Hamm said in a recent profile in GQ, that you had known how the show was going to end since the end of season one, that you guys would meet in a restaurant at the end of every season and talk it out—

No, not really. I mean, when I pitched the show I knew how it was going to end, I knew what was going to happen. I didn’t know how it was going to happen until between seasons four and five, and that’s when I told him the end game.

OK, and is that still true?

Did he say it was earlier than that? I don’t think it was. But I always share it with Jon, I mean Jon’s like—right after my wife, I tell Jon.

So it’s been true that you have this very real sense of the how it ends since season 4.

Yeah. But you know, I don’t want it to look like I’m keeping some giant twist or secret from the audience. It’s just a very organic story. It’s very much related to the way we’ve been telling the show the whole time.

One of the most common criticisms of the show is that it’s too slow, there’s too little action. Whereas I always rebut that it’s detail-oriented and sumptuous, you’re supposed to lean into it. But is that tension something you dealt with over the course of running the show?

It feels action-packed to me. It may not have enough action for people who are used to seeing someone defuse a bomb that’s going to blow up the entire world or come face-to-face with a dragon or even God or whatever. In terms of putting yourself as a real person into their lives, it’s got a lot of action.

Your daughter walking in on you having an affair with your neighbour? That is action. Losing your company, starting your own company, getting divorced, going to jail—even if it’s for the night—these are all things… I can’t even explain it. It’s happening on such a small scale. Is it slower-paced I guess than other shows? Probably, but it all depends on what you consider tension. Putting a gun in the scene means someone is going to get killed, and it will hold people’s attention. The show doesn’t have that, so you go to a meeting where someone is going to be embarrassed or fired, that’s the tension, and you have to enjoy the drama of knowing more than the characters, having the characters know more than each other sometimes, irony. This is a totally different set of tools.

That’s why I’m so spoiler-phobic, because the actual plot, even though it’s pretty elaborate, can be described in a couple of sentences. It’s how it happens, you know? I’ll use an episode for example. They’re trying to get North American Aviation—this is the episode “Hands and Knees”—and Don has filled out a form and is now going to be investigated by the government, and we know that he has this crime hanging over his head, he’s AWOL. Well, for Don and for Betty, the government coming to them in that era just after McCarthyism and World War II, it’s a big deal. You know, Joan is pregnant with another man’s baby, it’s a soap-opera journey, but in real life it happens all the time and it’s a scandal, it’s tense, whatever, but it’s not… in a way it’s not life-and-death.

Do you feel at this point you know the 1960s almost as well as you know the 2010s?

I don’t know. It’s kind of funny, I’m not a historian, but it’s been such an amazing experience of learning and having my intuition both confirmed and completely confounded. A lot of it was about revising people’s perception of it and trying to take it out of the newsreel cliché, and say, this is real, and how would it really be experienced. How do we experience history? We are not living in the front page. You can’t look at today’s newspaper and reconstruct even probably one conversation that you’re going to have today. The closest events I’ve lived through are Nixon’s resignation in my childhood, Watergate, certainly 9/11, the hostage crisis in Iran. There are days when the events are on everybody’s minds and it influences everything they do and there are days when if you’re getting divorced, that’s all that matters, you’re getting divorced. I don’t know about the ’60s per se. I think that I feel more of an expert on the complexities of the workplace and adulthood than I do on the ’60s. And the lesson being: I don’t know anything. You know what I mean? That’s true wisdom.

I’ve asked a lot about Don, but did you always know about, say, Peggy? Did you always want to build her up or did that just happen along the way?

Well, my pitch for the first season was always that Peggy would ascend completely by accident, that she would be discovered and she’s ambitious and that she would become good at this job. I didn’t even know Joan was a main character when I wrote the pilot, I didn’t know that until I met Christina Hendricks. I didn’t know Roger was going to live beyond that first season. I would love to take credit for having some grand plan, but we made these one season at a time and one episode at a time. And in season five, six, and this one, we still at the end of every year completely blew out all the story that we had and I would just say, “OK, well, what’s next?”

There was a conscious decision at the origin of the show that we would follow the calendar. The whole show could have taken place in some amorphous 1960s, you know, it could still be 1960. Everybody could still be dressed the same and time could never move on at all, and I decided to commit to that because I thought it would be amazing if we got to do 10 years in their life, if you could see how much their lives had changed and how much had gone on and how different they were than when they started—not more innocent when they started, but you’re just going to think that way because you just met them. And I got to tell the story of New York falling apart and language becoming cruder and the culture becoming cruder and the racial aspects changing, sex and gender issues changing. I knew that that could happen if we got to go on the whole time, so those things were kind of on my mind.

But no specifics, I hate to say it. I wish I could say that. I wasn’t like, “Hey, we’re gonna do the whole thing and at the end of the whole thing, you know, Joan’s gonna have Roger’s baby and get fired from the company that takes them.” I did, once I knew we had some time. I did enjoy telling the story of advertising in that period—that, I did commit to from the beginning. This self-named “creative revolution” and the business aspect to the story, which is those behemoth companies getting bigger then going public then acquiring other companies, then boutique agencies rising up, then them getting bought, people going public, mergers being forced on them and then finally everything ends up… now there’s like four advertising agencies in the whole world. That story was told when it happened, which was from 1959 to 1969.

Regardless of what happens to Don, his ghost is going to be hanging over you in a way. Are you ready for that? Are you ready for him to follow you in your life, no matter what indeed comes next?

I am very—at the risk of getting struck by lightning—I am extremely proud of the work we all did on this show, and it was drawn from our lives and from our parents’ lives and from a lot of strangers’ lives, and we tried to do a show about how hard it is to be a person and to kind of non-judgmentally reflect the reality of modern human life, and I’m super, super proud that people enjoyed that, and I’m very proud of anything that sticks to me for the rest of my life that has to do with this, you know? I don’t ever expect this to happen again, if that’s what you’re asking.

Thanks so much for taking the time today. And enjoy the finale, as it were!

I’m going to enjoy it, and I hope that people are aware of my special connection to Canada, which is that there are people in the United States who are very much aware that it’s there and the role it plays in our life [laughing].

Well, we’re very glad every time any American says that.

I mean it! It’s another one of those identity issues. It really is. To be Canadian, to have another nationality that is so invisible to us in many ways and yet not the same has been fascinating. I’ve loved playing with that. And I get it.

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